1,1-Dibromoethane → 2-(2-Bromoethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

HRID 544668Notes

Reaction equation

HRID 544668 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[S:12][C:11](=[S:22])[N:10]=2)=[CH:5][CH:4]=1.[Br:23][CH:24](Br)[CH3:25]>[OH-].[Na+]>[Br:23][CH2:24][CH2:25][S:22][C:11]1[S:12][C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 112011,1-DibromoethaneHCID 132096564,5-Bis-(p-methoxyphenyl)-thiazoline-2-thione

Product 1

HCID 204583302-(2-Bromoethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2.0 g of 4,5-bis-(p-methoxyphenyl)-thiazoline-2-thione are dissolved in 10.4 ml of 2 N sodium hydroxide solution. 2.3 g of dibromoethane are added and the mixture is stirred at room temperature for 4 hours. The organic layer is then removed, the aqueous phase is subsequently shaken with 10 ml of toluene, and the combined organic phases are washed twice with 5 ml of 2 N sodium hydroxide solution each time, dried over magnesium sulphate and concentrated to dryness by evaporation under reduced pressure. 2-(2-Bromoethylthio)-4,5-bis-(p-methoxyphenyl)-thiazole, Rf =0.65 (silica gel, toluene/ethyl acetate 10:1) is obtained.

Workup

  1. customThe organic layer is then removed
  2. stirringthe aqueous phase is subsequently shaken with 10 ml of toluene
  3. washthe combined organic phases are washed twice with 5 ml of 2 N sodium hydroxide solution each time
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness by evaporation under reduced pressure

Sources & evidence

ORD record
ord-04306c8c39a9436798350f8b937568aa
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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